That’s a sign that should be hanging in every MLB front office while they mull over potentially offering millions of dollars to players in free agency.
Spending money on free agents is a necessary evil in building a World Series contender, and there are inevitably going to be players who fail to live up to expectations whether it’s a result of injuries, regression or them simply being overpaid from the start.
Ahead we’ve highlighted each team’s biggest free agency flop since the 2000 season, based on production relative to expectations and the
Date: Dec, 17, 2019
Contract: Five years, $85 million
Madison Bumgarner was the highest-paid player on the D-backs roster during their unexpected run to the World Series in 2023. However, he didn’t play for the team after April 26 when he was released with a 10.26 ERA after four starts.
A workhorse ace during his 11 seasons with the San Francisco Giants, Bumgarner simply didn’t have much left in the tank by the time he reached free agency. He finished with a 5.23 ERA in 363.1 innings during his time in the desert, and the D-backs are still on the hook for another $14 million in 2024.
Date: Nov. 29, 2012
Contract: Five years, $75.25 million
Outfielder B.J. Upton had a 28-homer, 31-steal contract year for the Tampa Bay Rays in 2012, but it was accompanied by a lackluster .246/.298/.454 batting line and 169 strikeouts in 146 games.
Those red flags didn’t stop the Braves from paying top dollar over a five-year deal, and he went on to hit .198 with a 66 OPS+ and minus-1.8 WAR in two seasons in Atlanta before he was dumped on the San Diego Padres in a package deal with All-Star closer Craig Kimbrel.
Runner-Up: SP Kenshin Kawakami (Jan. 13, 2009)
Date: Jan. 21, 2016
Contract: Seven years, $161 million
Slugger Chris Davis tested free agency before finding his way back to the Baltimore Orioles on a massive seven-year, $161 million deal, so this one counts as a free-agent signing rather than an extension.
He had a 110 OPS+ and 38 home runs in the first season of his new contract, but things quickly devolved from there and he had an all-time awful season in 2018 (-3.3 WAR, 36.8 K%). He eventually called it quits late in the 2021 season, but the Orioles will still be paying him in 2025 after the final year of his contract was restructured and deferred.
Date: Nov. 25, 2014
Contract: Five years, $95 million
The Red Sox spent big to retool their offense during the 2014-15 offseason, moving quickly to sign Sandoval and Hanley Ramirez to a four-year, $88 million deal on the same day in late November.
Sandoval went on to hit .237 with a 71 OPS+ and minus-1.6 WAR in 161 games over three seasons with the Red Sox before he was released on July 19, 2017. He then found his way back to the San Francisco Giants where he re-emerged as a productive bench player while Boston paid the bulk of his salary.
Runner-Up: OF Rusney Castillo (Aug. 23, 2014)
